CA2223513A1 - Derives d'acide betulinique et leurs utilisations - Google Patents

Derives d'acide betulinique et leurs utilisations

Info

Publication number
CA2223513A1
CA2223513A1 CA002223513A CA2223513A CA2223513A1 CA 2223513 A1 CA2223513 A1 CA 2223513A1 CA 002223513 A CA002223513 A CA 002223513A CA 2223513 A CA2223513 A CA 2223513A CA 2223513 A1 CA2223513 A1 CA 2223513A1
Authority
CA
Canada
Prior art keywords
betulinic acid
substituted
group
acid derivatives
uses therefor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002223513A
Other languages
English (en)
Other versions
CA2223513C (fr
Inventor
Kuo-Hsiung Lee
Yoshiki Kashiwada
Fumio Hashimoto
Louis Mark Cosentino
Mark Manak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of North Carolina at Chapel Hill
Panacos Pharmaceuticals Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2223513A1 publication Critical patent/CA2223513A1/fr
Application granted granted Critical
Publication of CA2223513C publication Critical patent/CA2223513C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA002223513A 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations Expired - Fee Related CA2223513C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/463,071 1995-06-05
US08/463,071 US5679828A (en) 1995-06-05 1995-06-05 Betulinic acid and dihydrobetulinic acid derivatives and uses therefor
PCT/US1996/009485 WO1996039033A1 (fr) 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations

Publications (2)

Publication Number Publication Date
CA2223513A1 true CA2223513A1 (fr) 1996-12-12
CA2223513C CA2223513C (fr) 2009-03-24

Family

ID=23838749

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002223513A Expired - Fee Related CA2223513C (fr) 1995-06-05 1996-06-05 Derives d'acide betulinique et leurs utilisations

Country Status (10)

Country Link
US (1) US5679828A (fr)
EP (2) EP1397957A2 (fr)
AT (1) ATE275823T1 (fr)
AU (1) AU6328896A (fr)
CA (1) CA2223513C (fr)
DE (1) DE69633398T8 (fr)
DK (1) DK0857018T3 (fr)
ES (1) ES2231818T3 (fr)
PT (1) PT857018E (fr)
WO (1) WO1996039033A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US9868758B2 (en) 2014-06-30 2018-01-16 Hetero Labs Limited Betulinic proline imidazole derivatives as HIV inhibitors
US10370405B2 (en) 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors
US10533035B2 (en) 2015-02-09 2020-01-14 Hetero Labs Ltd. C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962527A (en) * 1995-03-21 1999-10-05 The Board Of Trustees Of The University Of Illinois Method and composition for treating cancers
US5869535A (en) * 1995-03-21 1999-02-09 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
EP0902685A1 (fr) * 1997-01-24 1999-03-24 Marigen S.A. Ultramicro-emulsions de concentres spontanement dispersibles renfermant des esters de triterpenes pentacycliques a activite antitumorale, antivirale et antiparasitaire
US5750578A (en) * 1997-02-11 1998-05-12 Regents Of The University Of Minnesota Use of betulin and analogs thereof to treat herpesvirus infection
EP0988311B9 (fr) * 1997-06-04 2004-12-15 Cornell Research Foundation, Inc. Derives de betulinol
US6670345B1 (en) * 1997-09-30 2003-12-30 Dabur Research Foundation Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid
US6048847A (en) * 1997-09-30 2000-04-11 Dabur Research Foundation Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this
US6228850B1 (en) * 1997-09-30 2001-05-08 Dabur Research Foundation Antiangiogenic activity of betulinic acid and its derivatives
ES2281960T3 (es) * 1998-03-02 2007-10-01 The University Of North Carolina At Chapel Hill Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso.
US6303589B1 (en) * 1998-12-08 2001-10-16 Micro Flo Company Pentacyclic triterpenes
US6369101B1 (en) 1999-02-26 2002-04-09 Regents Of The University Of Minnesota Therapeutic method to treat herpes virus infection
US6392070B1 (en) 1999-08-10 2002-05-21 Regents Of The University Of Minnesota Birch bark processing and the isolation of natural products from birch bark
EP1218402B1 (fr) * 1999-09-09 2004-05-26 Dabur Research Foundation Nouveaux derives d'acide betulinique presentant une activite antiangiogenese, procedes de production de ces derives et leur utilisation pour traiter une tumeur associee a l'angiogenese
CA2446748C (fr) * 2001-05-11 2011-03-08 University Of Ottawa Compositions anxiolytiques de marcgraviaceae contenant de l'acide betulinique ou des derives d'acide betulinique et procedes associes
US7365221B2 (en) * 2002-09-26 2008-04-29 Panacos Pharmaceuticals, Inc. Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
WO2004028455A2 (fr) * 2002-09-26 2004-04-08 Panacos Pharmaceuticals, Inc. Derives monoacyles de la betuline et de la dihydrobetuline, preparation et utilisation de ceux-ci
JP2006520756A (ja) * 2003-01-29 2006-09-14 パナコス ファーマシューティカルズ インコーポレーティッド ウイルスキャプシドスペーサーペプチド１タンパク質のプロセシングの破壊によるｈｉｖ−１複製の阻害
US7537765B2 (en) * 2003-01-29 2009-05-26 Panacos Pharmaceuticals, Inc. Inhibition of HIV-1 replication by disruption of the processing of the viral capsid-spacer peptide 1 protein
US7026305B2 (en) * 2003-04-14 2006-04-11 Meharry Medical College Anti-HIV agents with dual sites of action
RU2387665C2 (ru) * 2004-03-17 2010-04-27 Панакос Фармасьютикалз, Инк. Фармацевтические соли 3-о-(3', 3'-диметилсукцинил)бетулиновой кислоты
CN100591688C (zh) * 2004-03-17 2010-02-24 帕纳克斯医药公司 3-0-(3＇,3＇-二甲基琥珀酰基)桦木酸的药用盐
WO2005112929A2 (fr) * 2004-05-20 2005-12-01 Cornell Research Foundation, Inc. Activite anti vih-1 de derives de betulinol
AU2005245506A1 (en) * 2004-05-24 2005-12-01 Panacos Pharmaceuticals, Inc. Disruption of the processing of the viral capsid-spacer peptide 1 protein
US20060154903A1 (en) 2004-09-10 2006-07-13 Cornell Research Foundation, Inc. Betulinol derivatives as anti-cancer agents
TW200628161A (en) * 2004-11-12 2006-08-16 Panacos Pharmaceuticals Inc Novel betulin derivatives, preparation thereof and use thereof
ATE548043T1 (de) * 2005-04-12 2012-03-15 Myrexis Inc Polymorphe von 3-o-(3',3'- dimethylsuccinyl)betulinsäure-di-n-methyl-d- glucamin
JP2008543945A (ja) * 2005-06-22 2008-12-04 ミリアド ジェネティクス， インコーポレイテッド 抗ウイルス化合物
WO2007078848A2 (fr) * 2005-12-16 2007-07-12 Panacos Pharmaceuticals, Inc. Préparation de sels pharmaceutiques de l'acide 3-o-(3',3'-diméthylsuccinyl)bétulinique
WO2007114978A2 (fr) * 2006-02-09 2007-10-11 Boehringer Ingelheim International Gmbh Procédé destiné à traiter une infection au vih par une administration conjointe de tipranavir et de pa-457
US20070232577A1 (en) * 2006-03-23 2007-10-04 Advanced Life Sciences, Inc. Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
US20080039428A1 (en) * 2006-06-29 2008-02-14 Panacos Pharmaceuticals, Inc. Antiretroviral combination therapy
US20110144069A1 (en) * 2006-10-16 2011-06-16 Myriad Genetics, Incorporated Compounds for treating viral infections
TW200837074A (en) 2006-11-03 2008-09-16 Panacos Pharmaceuticals Inc Extended triterpene derivatives
US20110152229A1 (en) * 2006-11-22 2011-06-23 Duke University Betulinic acid derivatives as anti-hiv agents
MX2012013628A (es) 2010-06-04 2012-12-17 Bristol Myers Squibb Co Amidas c-28 de derivados del acido betulinico c-3 modificados como inhibidores de la maduracion del virus de inmunodeficiencia humana (vih).
BR112012030818A2 (pt) 2010-06-04 2019-09-24 Bristol-Myers Squibb Company "derivados de ácido c-3 betulínico modificado como inibidores da maturação do hiv"
RU2448115C1 (ru) * 2010-12-20 2012-04-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет (НГУ) Гидрированная бетулоновая кислота и ее амиды как противоопухолевые средства тритерпеновой природы
ES2552512T3 (es) 2011-01-31 2015-11-30 Bristol-Myers Squibb Company Aminas C-28 de derivados de ácido betulínico modificado en C-3 como inhibidores de la maduracion del virus de inmunodeficiencia humana
AU2012212509B2 (en) 2011-01-31 2016-01-21 ViiV Healthcare UK (No.4) Limited C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity
US8754069B2 (en) 2011-09-21 2014-06-17 Bristol-Myers Squibb Company Betulinic acid derivatives with antiviral activity
US8906889B2 (en) 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
US8889854B2 (en) 2012-05-07 2014-11-18 Bristol-Myers Squibb Company C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity
CN103768078B (zh) 2012-10-22 2019-02-05 北京大学 三萜衍生物及其抗流感用途
EA027371B1 (ru) 2013-02-06 2017-07-31 Бристол-Майерс Сквибб Компани C-19 модифицированные тритерпеноиды с ингибиторной активностью созревания вич
WO2014130810A1 (fr) 2013-02-25 2014-08-28 Bristol-Myers Squibb Company Dérivés d'acide bétulinique modifiés par alkyle et alcényle en c-3 utiles dans le traitement du vih
UY36070A (es) 2014-04-11 2015-10-30 Bristol Myers Squibb Company Una Corporación Del Estado De Delaware Triterpenoides con actividad inhibidora de la maduración de hiv
WO2015195776A1 (fr) 2014-06-19 2015-12-23 Bristol-Myers Squibb Company Dérivés d'acide bétulinique présentant une activité inhibitrice de maturation du vih
RU2017118489A (ru) 2014-11-14 2018-12-14 ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД Оксолупеновые производные
RU2017118576A (ru) 2014-11-14 2018-12-14 ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД C-17-арил-замещённые аналоги бетулиновой кислоты
PL227790B1 (pl) 2015-08-13 2018-01-31 Slaski Univ Medyczny W Katowicach Fosfoniany acetylenowych pochodnych betuliny o działaniu przeciwnowotworowym, sposób ich wytwarzania i zastosowanie.
AR107512A1 (es) 2016-02-04 2018-05-09 VIIV HEALTHCARE UK Nº 5 LTD Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1
CA3059291A1 (fr) * 2017-04-06 2018-10-11 Derm-Biome Pharmaceuticals Inc. Compositions et methodes de traitement d'une infection et nouvelles preparations cosmeceutiques
PL237998B1 (pl) 2018-05-28 2021-06-28 Narodowy Inst Lekow Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie
AU2019292599B2 (en) 2018-06-29 2022-03-03 Dfh Therapeutics Triterpene amine derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415601A (en) * 1973-03-14 1975-11-26 Biorex Laboratories Ltd Dihydrobetulinic acid derivatives
FR2683531B1 (fr) * 1991-11-13 1993-12-31 Rhone Poulenc Rorer Sa Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent.
US5643884A (en) * 1993-08-09 1997-07-01 Glycomed Incorporated Lupane triterpenoid derivatives

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US9868758B2 (en) 2014-06-30 2018-01-16 Hetero Labs Limited Betulinic proline imidazole derivatives as HIV inhibitors
US10533035B2 (en) 2015-02-09 2020-01-14 Hetero Labs Ltd. C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors
US11034718B2 (en) 2015-02-09 2021-06-15 Hetero Labs Limited C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors
US10370405B2 (en) 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors

Also Published As

Publication number Publication date
AU6328896A (en) 1996-12-24
ATE275823T1 (de) 2004-10-15
EP1397957A2 (fr) 2004-03-17
EP0857018A1 (fr) 1998-08-12
WO1996039033A1 (fr) 1996-12-12
CA2223513C (fr) 2009-03-24
DE69633398T8 (de) 2006-01-12
DE69633398T2 (de) 2005-09-22
EP0857018A4 (fr) 2002-10-23
DE69633398D1 (de) 2004-10-21
PT857018E (pt) 2005-01-31
DK0857018T3 (da) 2004-11-29
ES2231818T3 (es) 2005-05-16
US5679828A (en) 1997-10-21
EP0857018B1 (fr) 2004-09-15

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